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Relevant academic research and scientific papers

Ceramic boron carbonitrides for unlocking organic halides with visible light

Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is

Cellulose supported Pd(II) complex catalyzed carbon-carbon bonds formation

Corn-cobs are an agro-industrial waste and composed of cellulose mostly. In this study cellulose was isolated from the waste corn-cobs and modified to polymeric hydroxamic acid palladium complex 1 and characterized by using a variety of spectroscopic methods such as field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The complex 1 exhibited high catalytic activity towards Suzuki and Heck coupling reactions of activated and deactivated aryl halides to give the respective coupling products with high yield. Moreover, the complex 1 was recovered and recycled five times with no considerable loss of catalytic overall performance.

Delineating the Role of Substituents on the Coordination Behavior of Aroylhydrazone Ligands in PdII Complexes and their Influence on Suzuki–Miyaura Coupling in Aqueous Media

Reactions of piperonal aroylhydrazone ligands (HL1–HL4) with [PdCl2(PPh3)2] in CH3OH and CHCl3 afforded four new Pd(II) complexes (1–4) featuring diverse coordination behaviors. These complexes 1–4 were fully characterized by elemental analyses, UV/Visible, FT-IR and 1H/13C NMR spectra. The variant coordination modes of piperonal aroylhydrazone ligands with Pd(II) ion in these complexes were unambiguously confirmed by single-crystal XRD study. Though the ligands HL1–HL4 are of similar nature, one of them (HL4) possessing an electron withdrawing nitro group as substitution in the peripheral part of the hydrazone displayed an uncommon ligation towards the palladium ion. An experimentally observed molecular architects were in turn rationalized by density functional theory (DFT) calculations as well as natural bonding analysis (NBO). All these Pd(II) complexes were evaluated for their catalytic potential towards Suzuki–Miyaura cross-coupling reaction of sterically congested arylboronic acids with (hetero)arylhalides under an open-flask conditions in aqueous media with low catalyst loading. Advantageously, the selected catalyst was active up to five cycles without significant loss in activity.

Green synthesis of carbon quantum dots from vanillin for modification of magnetite nanoparticles and formation of palladium nanoparticles: Efficient catalyst for Suzuki reaction

In this report we prepared carbon quantum dots (CQD) from vanillin as an ecofriendly and naturally abundant compound for modification of magnetic nanoparticles (CQD@Fe3O4 NPs). This new magnetic solid has been used for complete reduction of PdCl2 with formation of stabilized palladium nanoparticles (Pd@CQD@Fe3O4 NPs) and characterized by SEM, TEM, EDX, solid UV, VSM, XPS, XRD, and N2 adsorption–desorption analyses. These magnetic supported Pd NPs have been used as an efficient catalyst for the Suzuki-Miyaura cross-coupling reactions of aryl bromides at room temperature in aqueous ethanol and of aryl chlorides at 120 °C in PEG200 under low catalyst loading in air. The heterogeneous catalyst can be easily recovered by an external magnet and reused for eight consecutive runs.

Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction

The Kumada-Corriu reaction is a powerful tool for C-C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent. The mechanistic reason for the effectiveness of this strategy is uncovered by continuous-infusion ESI-MS studies.

Palladacycles derived from arylphosphinamides for mild Suzuki-Miyaura cross-couplings

We present a type of palladacyclic complexes derived from arylphosphinamides which can be used as efficient and versatile precatalysts for mild Suzuki-Miyaura cross-coupling. With the presence of 1.0 mol% of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be very easily prepared through a two-step procedure from the readily affordable diphenyl-phosphinic chloride and exhibit excellent stability toward air and moisture. Due to these prominent properties, the new palladacycles would find practical use in Suzuki-Miyaura couplings.

Synthesis and Suzuki Reactions of N-Heterocyclic Carbene Difluoro(aryl)-boranes

Readily available NHC-arylboranes (NHC-BH2Ar) are converted in high yield to stable NHC-difluoro(aryl)boranes (NHC-BF2Ar) by treatment with 2 equiv of 1-chloromethyl-4-fluoro-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor). In turn, the NHC-difluoro(aryl)boranes participate directly in Suzuki reactions under conditions previously used for anionic trifluoroborate salts. Accordingly, NHC-difluoroboranes are a new class of stable precursors for Suzuki reactions.

Alkenes as alkyne equivalents in radical cascades terminated by fragmentations: Overcoming stereoelectronic restrictions on ring expansions for the preparation of expanded polyaromatics

Chemoselective interaction of aromatic enynes with Bu3Sn radicals can be harnessed for selective cascade transformations, yielding either Sn-substituted naphthalenes or Sn-indenes. Depending on the substitution at the alkene terminus, the initial regioselective 5-exo-trig cyclizations can be intercepted at the 5-exo stage via either hydrogen atom abstraction or C-S bond scission or allowed to proceed further to the formal 6-endo products via homoallylic ring expansion. Aromatization of the latter occurs via β-C-C bond scission, which is facilitated by 2c,3e through-bond interactions, a new stereoelectronic effect in radical chemistry. The combination of formal 6-endo-trig cyclization with stereoelectronically optimized fragmentation allows the use of alkenes as synthetic equivalents of alkynes and opens a convenient route to α-Sn-substituted naphthalenes, a unique launching platform for the preparation of extended polyaromatics.

Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for Suzuki-Miyaura cross-coupling reactions in water

The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.

Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for suzuki-miyaura cross-coupling reactions in water

The polystyrene-supported Pd(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermal analysis (TG-DTA). This heterogeneous Pd(II) catalyst works efficiently for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides in aqueous medium. The effect of base, and additives for the C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without significant loss in its catalytic activity.